Hydrochloric Acid → HCID 11955204, compound

HRID 2357937Notes

Reaction equation

HRID 2357937 reaction equation
[CH3:1][O:2][C:3]1[N:8]2[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=[C:7]2[C:6]([C:16]2[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=2)=[CH:5][CH:4]=1.[OH-].[Na+].Cl>>[F:14][C:12]([F:13])([F:15])[C:10]1[CH:11]=[C:7]2[C:6]([C:16]3[CH:17]=[CH:18][C:19](=[O:22])[NH:20][N:21]=3)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]2[N:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11955202HCID 11955202, compound

Product 1

HCID 11955204HCID 11955204, compoundYield 29.1%

Procedure

The compound of Example 209 (79.8 mg) and sodium m-nitrosulfonate (57.6 mg) were suspended in a 0.5 mol/L aqueous sodium hydroxide solution (5.00 mL). The suspension was refluxed for 8 hours. Subsequently, diluted hydrochloric acid was added to make the mixture acidic and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification of the residue by amino-silica gel column chromatography (ethyl acetate) afforded the title compound as a yellow powder (23.1 mg).

Workup

  1. temperatureThe suspension was refluxed for 8 hours
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvent and subsequent purification of the residue by amino-silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-1ad0f8b3f34942b0815c75dfc3352830
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

Loading…